WO2014081697A3 - Composés et compositions anthelminthiques et leur procédé d'utilisation - Google Patents

Composés et compositions anthelminthiques et leur procédé d'utilisation Download PDF

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Publication number
WO2014081697A3
WO2014081697A3 PCT/US2013/070731 US2013070731W WO2014081697A3 WO 2014081697 A3 WO2014081697 A3 WO 2014081697A3 US 2013070731 W US2013070731 W US 2013070731W WO 2014081697 A3 WO2014081697 A3 WO 2014081697A3
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WIPO (PCT)
Prior art keywords
anthelmintic compounds
compositions
bicyclic
heterocyclic group
compounds
Prior art date
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PCT/US2013/070731
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English (en)
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WO2014081697A2 (fr
Inventor
Charles Q. Meng
Alan Long
Scot Huber
Srinivas Reddy GURRALA
Douglas Edward Wilkinson
Gregory Pacofsky
Original Assignee
Merial Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Priority to CA2891926A priority Critical patent/CA2891926A1/fr
Priority to DK13803337.8T priority patent/DK2922845T3/en
Priority to SG11201503959VA priority patent/SG11201503959VA/en
Priority to LTEP13803337.8T priority patent/LT2922845T/lt
Priority to CN201380069056.6A priority patent/CN104884453B/zh
Priority to RS20181041A priority patent/RS57779B1/sr
Priority to PL13803337T priority patent/PL2922845T3/pl
Priority to NZ708350A priority patent/NZ708350A/en
Priority to SI201331155T priority patent/SI2922845T1/sl
Priority to EA201500557A priority patent/EA030814B1/ru
Priority to MX2015006266A priority patent/MX366041B/es
Priority to BR112015011441A priority patent/BR112015011441A2/pt
Priority to AP2015008449A priority patent/AP3965A/en
Priority to JP2015544098A priority patent/JP6506694B2/ja
Priority to EP18177835.8A priority patent/EP3428162B1/fr
Priority to EP13803337.8A priority patent/EP2922845B1/fr
Priority to KR1020157016407A priority patent/KR102151832B1/ko
Priority to AU2013348175A priority patent/AU2013348175B2/en
Application filed by Merial Limited filed Critical Merial Limited
Priority to ES13803337.8T priority patent/ES2689037T3/es
Publication of WO2014081697A2 publication Critical patent/WO2014081697A2/fr
Publication of WO2014081697A3 publication Critical patent/WO2014081697A3/fr
Priority to ZA2015/03481A priority patent/ZA201503481B/en
Priority to HK16103062.9A priority patent/HK1215028A1/zh
Priority to AU2017200135A priority patent/AU2017200135B2/en
Priority to CY20181100828T priority patent/CY1120549T1/el
Priority to HRP20181448TT priority patent/HRP20181448T1/hr
Priority to AU2018271343A priority patent/AU2018271343A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P33/10—Anthelmintics
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    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Quinoline Compounds (AREA)
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Abstract

La présente invention concerne de nouveaux composés anthelminthiques de formule (I) dans laquelle Y et Z représentent indépendamment un groupe carbocyclique bicyclique ou un groupe hétérocyclique bicyclique, ou l'un parmi Y ou Z représente un groupe carbocyclique bicyclique ou un groupe hétérocyclique bicyclique et l'autre parmi Y ou Z représente alkyle, alcényle, alcynyle, cycloalkyle, phényle, hétérocyclyle ou hétéroaryle, et les variables X1, X2, X3, X4, X5, X6, X7 et X8 sont telles que définies dans la description. L'invention concerne également des compositions vétérinaires comprenant les composés anthelminthiques de l'invention, et leurs utilisations pour le traitement et la prévention d'infections parasitaires chez des animaux.
PCT/US2013/070731 2012-11-20 2013-11-19 Composés et compositions anthelminthiques et leur procédé d'utilisation WO2014081697A2 (fr)

Priority Applications (25)

Application Number Priority Date Filing Date Title
ES13803337.8T ES2689037T3 (es) 2012-11-20 2013-11-19 Compuestos y composiciones antihelmínticas y procedimiento de utilización de los mismos
SG11201503959VA SG11201503959VA (en) 2012-11-20 2013-11-19 Anthelmintic compounds and compositions and method of using thereof
LTEP13803337.8T LT2922845T (lt) 2012-11-20 2013-11-19 Antihelmintiniai junginiai ir kompozicijos ir jų naudojimo būdai
CN201380069056.6A CN104884453B (zh) 2012-11-20 2013-11-19 驱蠕虫化合物和组合物和使用其的方法
RS20181041A RS57779B1 (sr) 2012-11-20 2013-11-19 Antihelmintska jedinjenja i kompozicije i postupak za njihovu upotrebu
PL13803337T PL2922845T3 (pl) 2012-11-20 2013-11-19 Związki przeciwrobacze oraz ich kompozycje i sposób stosowania
NZ708350A NZ708350A (en) 2012-11-20 2013-11-19 Anthelmintic compounds and compositions and method of using thereof
SI201331155T SI2922845T1 (sl) 2012-11-20 2013-11-19 Antihelmintske spojine in sestavki ter postopek za njihovo uporabo
EA201500557A EA030814B1 (ru) 2012-11-20 2013-11-19 Антигельминтные соединения, композиции и способы их применения
MX2015006266A MX366041B (es) 2012-11-20 2013-11-19 Compuestos antihelmínticos y composiciones y método de uso de los mismos.
BR112015011441A BR112015011441A2 (pt) 2012-11-20 2013-11-19 composições e compostos antihelmínticos e métodos de usos dos mesmos
AP2015008449A AP3965A (en) 2012-11-20 2013-11-19 Anthelminitic compounds and compositions and method of using thereof
JP2015544098A JP6506694B2 (ja) 2012-11-20 2013-11-19 駆虫性化合物及び組成物並びにこれらの使用方法
CA2891926A CA2891926A1 (fr) 2012-11-20 2013-11-19 Composes et compositions anthelminthiques et leur procede d'utilisation
EP13803337.8A EP2922845B1 (fr) 2012-11-20 2013-11-19 Composés et compositions anthelminthiques et leur procédé d'utilisation
KR1020157016407A KR102151832B1 (ko) 2012-11-20 2013-11-19 구충제 화합물 및 조성물 및 이의 사용 방법
AU2013348175A AU2013348175B2 (en) 2012-11-20 2013-11-19 Anthelmintic compounds and compositions and method of using thereof
EP18177835.8A EP3428162B1 (fr) 2012-11-20 2013-11-19 Composés et compositions anthelminthiques et leur procédé d'utilisation
DK13803337.8T DK2922845T3 (en) 2012-11-20 2013-11-19 ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND PROCEDURES FOR USE THEREOF
ZA2015/03481A ZA201503481B (en) 2012-11-20 2015-05-18 Anthelmintic compounds and compositions and method of using thereof
HK16103062.9A HK1215028A1 (zh) 2012-11-20 2016-03-16 驅蠕蟲化合物和組合物和使用其的方法
AU2017200135A AU2017200135B2 (en) 2012-11-20 2017-01-09 Anthelmintic compounds and compositions and method of using thereof
CY20181100828T CY1120549T1 (el) 2012-11-20 2018-08-09 Ανθελμινθικες ενωσεις και συνθεσεις και μεθοδος χρησης αυτων
HRP20181448TT HRP20181448T1 (hr) 2012-11-20 2018-09-11 Antihelmintski spojevi i sastavi te postupak za njihovu uporabu
AU2018271343A AU2018271343A1 (en) 2012-11-20 2018-11-29 Anthelmintic compounds and compositions and method of using thereof

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US201261728782P 2012-11-20 2012-11-20
US61/728,782 2012-11-20

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